John F. Kennedy's political career began long before he was elected president. In fact, one could argue that his journey to the White House actually began long before he was even born, in the halls of Boston's State Building in 1892, when his maternal grandfather, John Fitzgerald, first took office as a Massachusetts state senator. Fitzgerald, the son of Irish immigrants, proved early in his career to be a natural politician and was nicknamed "Honey Fitz" for his geniality, charm, and manipulative skills. A popular verse from the 1890s went: "Honey Fitz can talk you blind / on any subject you can find / Fish and fishing, motorboats / Railroads, streetcars, getting votes."2 Following his term in the state senate, Fitzgerald successfully ran for Congress in 1894 and mayor of Boston in 1906. Despite his popularity in the Boston political scene, Honey Fitz was notorious for corrupt dealings and nepotism. In his 1918 bid for the US Senate, Honey Fitz eked out a narrow victory (a margin of 238 votes!) by falsely registering voters and hiring a large group of Italian immigrants—including a few professional boxers—to intimidate his opponent's supporters.3 Although Congress discovered these illegal tactics and voted to unseat Honey Fitz, this "ends justify the means" approach to politics would remain firmly ingrained in the Kennedy family ethos.
John F. Kennedy also inherited his knack for politics from his ambitious and shrewd father, Joseph Kennedy (a.k.a. Joe Sr.). The son of a well-to-do banker and state politician, Joseph was a precocious student and successful businessman. After graduating from Harvard, Joe made his millions as a bank president (a position he first held at the tender age of 25), stock trader, and movie producer. He married Honey Fitz's daughter, Rose, in 1914, thereby uniting two of Boston's most prominent Irish Catholic families. Joe's political career took off in 1932, when he began campaigning and fundraising for presidential hopeful Franklin Delano Roosevelt. Following FDR's victory, Joe was appointed Chairman of the powerful Securities Exchange Commission in 1934 and U.S. Ambassador to England in 1937. Though Joseph Kennedy was a lifelong gambler and philanderer—an affair with actress Gloria Swanson in 1920 almost destroyed his marriage—he was also an unrelentingly smart political strategist who pushed his sons toward public office.